Triethylamine → (+)-cis-2-(4-methoxyphenyl)-3-(4-chloro-2-nitrobenzoyloxy)-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate

HRID 1247992Notes

Reaction equation

HRID 1247992 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[C@@H:28]([OH:29])[C:27](=[O:30])[N:26]([CH2:31][CH2:32][N:33]([CH3:37])[CH2:34][CH2:35][CH3:36])[C:25]3[CH:38]=[CH:39][CH:40]=[CH:41][C:24]=3[S:23]2)=[CH:18][CH:17]=1.C(N(CC)CC)C.[C:49]([O-:54])(=[O:53])[C:50]([O-:52])=[O:51]>C(Cl)Cl>[C:49]([OH:54])(=[O:53])[C:50]([OH:52])=[O:51].[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:22]2[C@@H:28]([O:29][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=3[N+:11]([O-:13])=[O:12])[C:27](=[O:30])[N:26]([CH2:31][CH2:32][N:33]([CH3:37])[CH2:34][CH2:35][CH3:36])[C:25]3[CH:38]=[CH:39][CH:40]=[CH:41][C:24]=3[S:23]2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 71081OxalateHCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 70381919(+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 70491012(+)-cis-2-(4-methoxyphenyl)-3-(4-chloro-2-nitrobenzoyloxy)-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalateYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.88 g of 4-chloro-2-nitrobenzoyl chloride in 3 ml of methylene chloride is added to a mixture of 1.34 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 15 ml of methylene chloride and 0.5 ml of triethylamine. The mixture is treated in the same manner as described in Example 30-(2). The crude product is converted to its oxalate and then recrystallized from ethanol. 1.78 g of (+)-cis-2-(4-methoxyphenyl)-3-(4-chloro-2-nitrobenzoyloxy)-5-[2-(N-methyl-N-n-propylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate are thereby obtained as colorless plates. Yield: 79.5%.

Workup

  1. additionThe mixture is treated in the same manner
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fee06cfd20d54786ad9aac7542781c82
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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